Hydrochloric Acid → N-Methacryloyl-5-aminosalicylic acid

HRID 1070372Notes

Reaction equation

HRID 1070372 reaction equation
[C:1](O)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(OC(Cl)=O)C.C(N(CC)CC)C.[NH2:20][C:21]1[CH:29]=[C:25]([C:26]([OH:28])=[O:27])[C:24]([OH:30])=[CH:23][CH:22]=1.Cl>C(#N)C>[C:26]([C:25]1[CH:29]=[C:21]([NH:20][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH:22]=[CH:23][C:24]=1[OH:30])([OH:28])=[O:27]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 40755-Aminosalicylic AcidHCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 171252N-Methacryloyl-5-aminosalicylic acidYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Into a 1 liter flask were added 600 ml of acetonitrile, 95.2 g (1.1 mol) of methacrylic acid and 120.1 g (1.1 mol) of chloroformic acid ethyl ester. To this mixture 111.8 g (1.1 mol) of triethylamine was added over a period of 1 hour in a cold bath. Stirring was continued for 1 hour at room temperature and 141.2 g (1 mol) of 5-aminosalicylic acid was added. The mixture was heated for 2 hours at 60° C. The mixture was poured into 5 liter of 1% HCl solution. The deposit was filtered, washed and dried to produce 164.7 g of N-(3-carboxy-4-hydroxyphenyl)methacrylamide.

Workup

  1. filtrationThe deposit was filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-951222f37f934a7984e42aff27eff827
Source dataset
uspto-grants-2005_06
Patent number
US06902860B2

Reaction notes

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